Three new compounds from endophytic fungus Periconia sp. F-31

doi:10.5246/jcps.2020.04.023

Abstract

Abstract:

Three new compounds (1–3), includinga chlorine-containing dihydroisocoumarin pericochlorosin A (1), a chlorinated phenol pericochlorosin B (2) and a decalin derivative pericoannosin G (3), were isolated from endophytic fungus Periconia sp. F-31 of the medicinal plant Annona muricata. The structures and absolute configurations were elucidated by extensive spectroscopic methods and calculated electronic circular dichroism analysis. Compound 2 displayed potent anti-HIV activity with IC₅₀ value of 2.2 μM.

Key words: Endophytic fungus, Periconia, Pericochlorosin, Pericoannosin

CLC Number:

R284

Supporting:

1. ECD and OR Calculations of 3

Since the relative configuration of 3 was established by the NOESY spectrum, only two stereoisomers existed: (2R, 3S, 8S, 11R)-3a and (2S, 3R, 8R, 11S)-3b(Figure S1). Conformational analysis of 3a was carried out via Monte Carlo searching with the MMFF94 molecular mechanics force field using the Spartan14 software.¹ Conformational analyses of 3a showed 4 conformers having relative energy within 10 kcal/mol were considered for further DFT calculations at B3LYP/6-31+G (d, p) level in methanol (Figure S2). Subsequently, the conformers were re-optimized using DFT at the WB97XD/DGDZVP level in methanol with the Gaussian 09 program.² (Tables S1). The WB97XD/DGDZVP harmonic vibrational frequencies were further calculated to confirm their stability. Those stable conformers with their Boltzmann distribution (>1%) also were carried out at the TDDFT CAM-B3LYP/DGDZVP, and B3LYP/6-311++G (2d, p) level in the methanol for ECD and OR computation, respectively. Boltzmann statistics were performed for ECD simulations with a standard deviation of σ 0.3 Ev. The final ECD spectra and OR value of 3a were obtained according to the Boltzmann distribution theory and their relative Gibbs free energy (ΔG), respectively. In the region of 200–400 nm, the theoretically calculated ECD spectrum of 3a was agreed with the experimental ECD spectrum of 3 (Figure S2). The experimental OR value of 3 (+15.0) was in good agreement with the theoretically calculated OR value of 3a (+194.4, Table S2) but was opposite in sign to that of 3b (–194.4) in methanol.

Figure S1. The structure of 3 (3a and 3b)

Figure S2. WB97XD/DGDZVP optimized 4 lowest energy 3D conformers of 3a

Table S1.Free energies (ΔG), and Boltzmann distribution abundances of conformers of 3a

Table S2. Calculated OR Values of the Lowest Energy Conformers of 3a.

^aAveraged according to the Boltzmann-calculated contribution at WB97XD/DGDZVP level.

References

(1) Spartan 14, Wavefunction, Inc.: Irvine, CA.

(2) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc., Wallingford CT, 2010.

2. NMR, MS, IR, UV, CD spectra of compounds 1–3

Figure S3. ¹H NMR spectrum of compound 1.

Figure S4. ¹³C NMR spectrum of compound 1.

Figure S5. DEPT spectrum of compound 1.

Figure S6. HSQC spectrum of compound 1.

Figure S7. HMBC spectrum of compound 1.

Figure S8. ESIMS spectrum of compound 1.

Figure S9. HRESIMS spectrum of compound 1.

Figure S10. IR spectrum of compound 1.

Figure S11. UV spectrum of compound 1.

Figure S12. ECD spectrum of compound 1

Figure S13. ¹H NMR spectrum of compound 2.

Figure S14. ¹³C NMR spectrum of compound 2.

Figure S15. DEPT spectrum of compound 2.

Figure S16. HSQC spectrum of compound 2.

Figure S17. HMBC spectrum of compound 2.

Figure S18. ESIMS spectrum of compound 2.

Figure S19. HRESIMS spectrum of compound 2.

Figure S20. IR spectrum of compound 2.

Figure S21. UV spectrum of compound 2.

Figure S22. ECD spectrum of compound 2.

Figure S23. ¹H NMR spectrum of compound 3.

Figure S24. ¹³C NMR spectrum of compound 3.

Figure S25. DEPT spectrum of compound 3.

Figure S26. HSQC spectrum of compound 3.

Figure S27. ¹H-¹H COSY spectrum of compound 3.

Figure S28. HMBC spectrum of compound 3.

Figure S29. 1D-NOE spectrum of compound 3.

Figure S30. NOESY spectrum of compound 3.

Figure S31. HRESIMS spectrum of compound 3.

Figure S32. IR spectrum of compound 3.

Figure S33. UV spectrum of compound 3.

Figure S34. ECD spectrum of compound 3.

Jimei Liu, Minghua Chen, Ridao Chen, Kebo Xie, Dawei Chen, Shuyi Si, Jungui Dai. Three new compounds from endophytic fungus Periconia sp. F-31[J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(4): 244-251.

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